The short has also turned him into an unlikely Internet phenomenon. After the jump, Bolton talks about his collaboration with Lonely Island-ers Andy Samberg, Jorma Taccone and Akiva Schaffer, his new CD of duets, and why he won’t be dressing in drag again any time soon.

Entertainment Weekly: How did the digital short come about?
Michael Bolton: The Lonely Island guys reached out to my management and said they wanted to do this. I said, “I love those guys. But what are they thinking?” I was automatically scanning through my memory banks of the most wicked language and visuals. You want to work with guys like this. But at the same time I get invitations to perform at the Vatican! [Laughs] It could be potentially uncomfortable. And in the first few approaches some of the language was just so intense and off-color.

Could you give an example of that?
I can’t! [Laughs] Not right now. If you’ve seen the Natalie Portman sketch you know their brand is shock-funny, in that order. They love to get you where you just can’t believe what you’re looking at and then hit you with the funny. I’ve been all about humor and all about laughing since I was a kid. That’s just who I am. I’ve been kicked out of every class. Andy and I were talking about that. Neither one of us had our Bar Mitzvah because we couldn’t take Hebrew school seriously.

You could have a joint one now!
Now, there’s a funny video right there. That’s something I would need to talk to Andy about. But they were sending me lyrics and I was reading them and I was thinking, “This is funny.” Then I’d get to another line that I really wish I could share with you right now, but I just can’t. I would say, “Nope, I don’ t think I could be intoxicated enough to read this line.” It kept transforming. And they really wanted me to do it. Because they could have just said at any point, “Nah, you’re going to take the funny out of it, you’re going to take the shock value out of it.” Finally, I said “This is great. But can we still take a look at some of this language, because I’m still not comfortable. Scarface is Scarface. He can say pretty much anything. As my own character, I just have a rough time wrapping my head around it.”

How much input did you have into the music? The hooks really are quite Bolton-esque.
They came up with the music. They created this big giant hook. I’m sure they felt, “Hey, this is a Bolton kind of hook,” in their minds. I just sang it in a studio in Atlanta on a night off. The guys were on through Skype. They’re serious about their comedy but they’re really serious about the details. They were focused on the minutiae that great record producers focus on, not comedy writers. And I love seeing that work ethic. These guys were inspiring.

What was the shoot like?
They were 16 to 18 hour days, both days. There’s a tremendous amount of energy and focus that goes in to making these. And this one, they seemed to be going above and beyond. The shots of the ocean were at Brighton Beach and trucks descended and cranes came out. I thought, “Wow, these guys are making a movie here.” Now, it’s kind of gone off the charts. It’s the number one viewed clip around the world. I love the timing of it as well. Their CD is about to come out tomorrow. Then my CD, Gems, comes out June 21. I didn’t have a clue this would air so much or be received so well. My CD is an album of duets with people like Orianthi, and Delta Goodrem, and Seal, and Rascal Flatts. I don’t know if we’re going to have to put “Jack Sparrow” in the set.

Isn’t it too late to do that?
It’s too late to put it on this first initial pressing. It’s funny, the guys are talking about touring. They offered to come up on stage if we wanted to do it live. I said, “Be careful what you ask for, because I will take you up on that.”

You dressed in drag as Julia Roberts in Erin Brockovich. I don’t think it’s an insult to suggest that you are a better looking man than you are a woman.
[Laughs] I was terrified to look in the mirror. I tried to avoid it. I noticed when they were finishing me up as Erin that the crew started reacting in this really uncomfortable way. As I walked past, people were clearly uncomfortable. At one point I was breastfeeding the baby. You didn’t see that, I don’t think.

There’s also a scene where, as Tony Montana, you’re surrounded by what I assume is fake cocaine.
I assure you that—aside from the fact that I don’t think any one of us would be around a pile of coke—that they didn’t have it in the budget for that to be anything but some sort of baking powder. But it was pretty funny. And that’s one of my favorite movies. That’s one of my favorite characters Pacino ever brought to life. It was another one where you knew you were going to get hard laughs, especially once my head got dropped into that pile, that mountain of cocaine.

How on earth can you sing along to lines like “Davy Jones!” or “Giant Squid!” while keeping a straight face?
You have to, that’s the whole thing. During the rehearsals, there were times when nobody could keep a straight face. But the whole thing only pays off if you keep a straight face and deliver from a seriously committed place, which was not a problem at all with Jack Sparrow and Scarface. With Erin, I just kind of wanted to get those clothes off and take a shower.

Are you actually a fan of the Pirates movies?
I enjoy them, I do. It’s been written many times that Johnny kind of created his character primarily from Keith Richards. He lives not far from me in Connecticut.

So next time you bump into him, are you going to mention that you did this?
I haven’t bumped into him yet. I have a feeling that there’s so much more that I would like to talk to him about, since I’m a Stones fan. When I was 13, the first time they came over to America, I went to see him at New Haven Arena. I have a feeling there’s going to be a lot of things to talk about. But I will get around to Captain Jack Sparrow.

You can check out the (expletive-featuring) “Jack Sparrow” sketch below.